Ammonia → 1-Naphthylamine

HRID 1414435Notes

Reaction equation

HRID 1414435 reaction equation
[C:1]1(S([O-])(=O)=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[K+].[NH2-:16].[Na+].N>>[C:1]1([NH2:16])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 24533Sodium amideHCID 23663688Potassium naphthalene-1-sulphonate

Product 1

HCID 86401-NaphthylamineYield 86.8%

Procedure

In a 200-ml autoclave were placed 28.3 grams (0.115 mole) of anydrous potassium 1-naphthalene sulfonate, 9.7 grams (0.241 mole) of sodium amide and 105 ml of liquid ammonia in the same manner as in Example 1. The resultant mixture was heated at 110° C for 10 hours. The reaction pressure in the autoclave was 75 atm. during the reaction. After the ammonia was removed, 10 ml of water was added to the reaction mixture for hydrolysis. The product was extracted with ether and the ether was distilled off to produce crude 1-naphthyl amine. Recrystallization from ethanol gave 14.3 grams of 1-naphthyl amine having a melting point of 48° to 49° C. Yield ws 87.0%.

Workup

  1. customThe reaction pressure in the autoclave
  2. customduring the reaction
  3. customAfter the ammonia was removed
  4. addition10 ml of water was added to the reaction mixture for hydrolysis
  5. extractionThe product was extracted with ether
  6. distillationthe ether was distilled off
  7. customto produce crude 1-naphthyl amine
  8. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-85d53bd330a84234862b51fc358c717d
Source dataset
uspto-grants-1977_01
Patent number
US04001313

Reaction notes

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